“I really do have a rule now that if you’re going to wear a shirt, you should know at least three or four songs by the band,” says Alessandra Brawn. I’m chatting with the vivacious co-owner of Chapel—the de facto destination for enviable “Where-did-you-get-that?” vintage band T-shirts that Kanye West and Rihanna have sported to rumpled perfection—about the not-so tacit rules she’s developed on the job. “So I’m not a huge Iron Maiden fan but I specifically set myself down and was like, ‘All right, you gotta listen to a bunch of music and, you gotta read the Wikipedia page, you gotta really inform yourself because if someone calls you on it, you’re ready,” she continues. “So a part of my job description now is learning all the music of these different artists.”

Street cred aside, it’s a logical tenant to dress by, especially considering Brawn has surrounded herself with Chapel’s significant and covetable archive of obscure and rare band T-shirts. Since leaving her public relations post at Kiki de Montparnasse earlier this year she’s become a quick study in the world of vintage-tee devotion. She transformed the home office and library of the Soho apartment she shares with her husband and Chapel co-owner, Jon Neidich, into the company’s showroom. Besides adding to her personal trove of Elvis, David Bowie, and Prince tees, Brawn has been working closely with Chapel founder Patrick Matamoros and her husband to launch an online store. More than ten years ago, Matamoros was selling the shirts on a corner in Soho and but after striking up a relationship with Neidich (a frequent customer) and Brawn, the three decided to go into business together. “The charm of Chapel in a lot of ways was this sort of underground-ness of it. You had to know someone who knew, a ‘You-gotta-talk-to-my-T-shirt-guy’ kind of thing,” Brawn says. “Which is great, but it’s obviously not a sustainable business model to constantly be taking a suitcase to someone’s house or setting up on a street corner.”

It didn’t help that Matamoros was occasionally arrested for selling his rarefied tees of Run–D.M.C., Grateful Dead, and Sex Pistols, without a merchant’s license. Scourged from the Rose Bowl flea market and varied rag houses, his in-demand and somewhat renegade supply nevertheless made its way into the hands of major celebrity stylists and on the backs of their clients: Kanye West, Rihanna, A$AP Rocky, and Kim Kardashian, to name a few. After racking up a discerning club of insiders, the brand is now tasked with the challenge of preserving that elusive, exclusive feeling in an online context. At the suggestion of Matamoros’s past collaborator and mentor of sorts, Fear of God’s Jeremy Lorenzo, Chapel will feature online “drops.” “We’re releasing a limited number of T-shirts at a time online, and then of course we have a pretty substantial inventory out of our showroom, so if someone wanted to really come in and dig through the shirts, they are welcome to do so if they’re in New York,” says Brawn. “The site will also allow users to customize their search, a function that both helps the team to zero in on trends and assist their clients in the quest for a perfect Lil' Kim tee from the mid-’90s. To tap into the current fever for festival style, the brand plans to curate online releases around say, “Oldchella,” pulling shirts from particular artists. “There is nothing better than people running after you at a show going, ‘Where did you get your T-shirt?!’” Brawn says. “That’s our spin on festival attire.”

That rubric also crosses over to Brawn’s personal style. “I don’t want to look like I’m wearing a costume, so I like to mix something higher-end, like a pair of Balenciaga leather pants and a cool pair of designer heels,” she says. In the office, it’s all about Re/Done jeans with her The Last Waltz T-shirt score; for meetings, she’ll add a pair of nice earrings and heels. But Brawn knows all too well the Chapel tees are incredibly versatile and can be worn in varying ways. “To each their own,” she says. “Everyone styles them in their own unique way and it’s kind of fun to see how it’s worn, to see Rihanna wear one as a dress and someone else wear one under a really tailored blazer. It can go in any direction.”